The present invention relates to novel amido, cycloamido, carbonylamido, sulfonylamido, p-substituted phenoxy derivatives of 9-deoxy-9-methylene-PGF-type acids. These 9-deoxy-9-methylene-PG-type acids are known to be structural and pharmacological analogs of the prostaglandins. Further, novel 16-phenyl-9-deoxy-9-methylene-PGF-type compounds are described herein as such.
The prostaglandins are a family of 20 carbon atom fatty acids, being structural derivatives of prostanoic acid, which exhibit useful activity in a wide variety of biological systems. Accordingly, such prostaglandins represent useful pharmacological agents in the treatment and prevention of a wide variety of disease conditions.
Likewise, 9-deoxy-9-methylene-PGF-type compounds represent pharmacological agents exhibiting improved utility as compared to the known prostaglandins. Most especially, these 9-deoxy-9-methylene-PGF-type compounds are employed as regulators of mammalian fertility and procreation (being estrus or menstral cycle regulators, labor inducers, abortafacients) and anti-asthma and antithrombotic agents.
The preparation of 9-deoxy-9-methylene-PGF-type compounds is described in U.S. application Ser. No. 682,848, filed May 4, 1976, now U.S. Pat. No. 4,060,534, the disclosure of which is incorporated by reference herein. Particularly, there are described therein the preparation of all but the novel 16-phenyl-9-deoxy-9-methylene-PGF-type compounds whose preparation is described hereinafter.
In addition to the above art, which is descriptive of methods for preparing acids or ester derivatives, as well as C-1 alcohols or C-1 amines, of certain prostaglandin type compounds, the preparation of prostaglandin-type amides is likewise accomplished by known methods. For example, see U.S. Pat. No. 3,981,868, issued Sept. 21, 1976, for description of the preparation of certain amido and cycloamido derivatives of 11-deoxy-PG-type compounds.
Further, U.S. Pat. No. 3,954,741, issued May 4, 1976, describes the preparation of certain carbonylamido and sulfonylamido derivatives of various prostaglandin analogs.
Finally, see U.S. Pat. No. 3,890,372, issued June 17, 1975 for a description of the preparation of various p-substituted phenoxy derivatives (i.e. p-substituted phenyl esters) of various prostaglandins.